US3637777A - Organotin bis(monoorgano maleates) - Google Patents

Organotin bis(monoorgano maleates) Download PDF

Info

Publication number: US3637777A
Authority: US; United States
Prior art keywords: compositions; bis; vinyl halide; organotin; grams
Prior art date: 1969-02-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

US796900A

Other languages

English (en)

Inventor

Samuel Hoch

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Evonik Corp

Original Assignee

Tenneco Chemicals Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1969-02-05

Filing date

1969-02-05

Publication date

1972-01-25

1969-02-05 Application filed by Tenneco Chemicals Inc filed Critical Tenneco Chemicals Inc

1972-01-25 Application granted granted Critical

1972-01-25 Publication of US3637777A publication Critical patent/US3637777A/en

1982-12-30 Assigned to CHASE COMMERCIAL CORPORATION reassignment CHASE COMMERCIAL CORPORATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NUODEX, INC.

1983-03-28 Assigned to NUODEX INC., A CORP OF DE. reassignment NUODEX INC., A CORP OF DE. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: TENNECO CHEMICALS, INC.

1985-08-21 Assigned to NUODEX INC., TURNER PLACE, PO BOX 365, A CORP. OF DE. reassignment NUODEX INC., TURNER PLACE, PO BOX 365, A CORP. OF DE. RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: CHASE COMMERCIAL CORPORATION

1989-01-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000002688 maleic acid derivatives Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 abstract description 17
239000007788 liquid Substances 0.000 abstract description 17
239000003381 stabilizer Substances 0.000 abstract description 14
229920000915 polyvinyl chloride Polymers 0.000 abstract description 8
239000004800 polyvinyl chloride Substances 0.000 abstract description 8
239000011342 resin composition Substances 0.000 abstract description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
239000000203 mixture Substances 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
-1 vinyl halide Chemical class 0.000 description 19
229920002554 vinyl polymer Polymers 0.000 description 17
WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 15
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 13
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 13
239000011347 resin Substances 0.000 description 12
229920005989 resin Polymers 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000005020 hydroxyalkenyl group Chemical group 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
230000001050 lubricating effect Effects 0.000 description 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000014509 gene expression Effects 0.000 description 2
239000004014 plasticizer Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
HDIFHQMREAYYJW-FMIVXFBMSA-N 2,3-dihydroxypropyl (e)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C\CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-FMIVXFBMSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
DKGXIVRSAKPDHF-UHFFFAOYSA-N 6-chloro-3-methyl-1-phenylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)C=C(Cl)N1C1=CC=CC=C1 DKGXIVRSAKPDHF-UHFFFAOYSA-N 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000004709 Chlorinated polyethylene Substances 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
239000006057 Non-nutritive feed additive Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 1
229920001328 Polyvinylidene chloride Polymers 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000004049 embossing Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012760 heat stabilizer Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
CFSSWEQYBLCBLH-UHFFFAOYSA-N iso-hexadecyl alcohol Natural products CC(C)CCCCCCCCCCCCCO CFSSWEQYBLCBLH-UHFFFAOYSA-N 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000005498 polishing Methods 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
239000005033 polyvinylidene chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
239000003017 thermal stabilizer Substances 0.000 description 1
229940117958 vinyl acetate Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages

Definitions

This invention relates to stabilizers for vinyl halide resins and to resinous compositions stabilized therewith. More particularly, it relates to stabilized rigid polyvinyl chloride resin compositions that are characterized by excellent heat stability, color, and clarity.
Organotin compounds are Widely used as heat stabilizers for vinyl halide resins. Since most of these compounds do not have lubricating properties, they are ordinarily used in combination with lubricants so that the resinous compositions can be processed satisfactorily at elevated temperatures.
organotin compounds that have lubricating properties and hence can be used with very small amounts of lubricant or no added lubricant are the di-n-butyltin (monoalkyl maleates) in which the alkyl group has from 16 to 18 carbon atoms arranged in a straight chain.
These compounds are not completely satisfactory as stabilizers for vinyl halide resin compositions because at room temperature they are Waxy solids that are difiicult to handle. In addition they impart an undesirable haze to the finished resinous sheets because they are not completely compatible with vinyl halide resins.
liquid organotin compounds are excellent thermal stabilizers for vinyl halide resins, These low-viscosity liquids have excellent handling characteristics. They have lubricating properties that are in many cases superior to those of the aforementioned di-n-butyltin (monoalkyl maleates). Because these organotin compounds are completely compatible with polyvinyl chloride and other vinyl halide resins, compositions containing them can be formed into sheets that show little or no haze. In addition compositions stabilized with these liquid organotin compounds have excellent thermal stability, excellent color and color retention, and other valuable properties.
liquid organotin stabilizers of this invention have the structural formula wherein each R represents a branched-chain alkyl group having from 16 to 18 carbon atoms, an alkenyl group having from 16 to 18 carbon atoms, or a hydroxy alkenyl group having from 16 to 18 carbon atoms.
R represents a branched-chain alkyl group having from 16 to 18 carbon atoms, an alkenyl group having from 16 to 18 carbon atoms, or a hydroxy alkenyl group having from 16 to 18 carbon atoms.
Illustrative of these liquid organotin compounds are the following:
di-n-butyltin bis (mono-Z-hexyldecyl maleate), di-n-butyltin bis (mono-Z-octyldecyl maleate) di-n-butyltin bis (mono9-octadecen-1-yl maleate), di-n-butyltin bis (mono-8-heXadecen-1-yl maleate), di-n-butyltin bis (mono-l2-hydroxy-9-octadecen-l-yl maleate), di-n-butyl bis (mono-16-hydroxy-7-hexadecenl-yl maleate), and the like.
liquid organotin compounds or a mixture of two or more of them may be present in the stabilized resin compositions of this invention.
the liquid organotin compounds may be prepared by any suitable and convenient procedure. For example, they may be prepared by heating the appropriate monoester of maleic acid with di-n-butyltin oxide. This reaction is generally carried out in a solvent, such as benzene, toluene, or xylene.
a solvent such as benzene, toluene, or xylene.
liquid organotin compound need be present in the stabilized compositions of this invention. It has been found that as little as 1 percent of the stabilizer, based on the weight of the vinyl halide resin, will bring about an appreciable improvement in the heat stability of the composition. Approximately 10 percent or more of the stabilizer can be used, but these larger amounts generally do not provide further improvement in the properties of the resinous compositions and for this reason are not ordinarily used. In most cases approximately 2 percent to 5 percent of the stabilizer, based on the weight of the vinyl halide resin, gives most advantageous results.
This invention is of particular value in the stabilization of rigid polyvinyl chloride composition, that is, compositions which are formulated to Withstand temperatures of at least 350 F.
the novel stabilizers can also be used in plasticized vinyl halide resin compositions of conventional formulation Where high softening point is not a requisite.
the vinyl halide resins that may be employed in such compositions include both vinyl halide homopolymers, such as polyvinyl chloride, polyvinyl bromide, and polyvinylidene chloride and copolymers, such as those formed by the polymerization of a vinyl halide with up to about 30 percent of a comonomer, such as vinyl ace tate, vinyl propionate, vinylidene chloride, styrene, methyl methacrylate, ethylene, and the like.
a comonomer such as vinyl ace tate, vinyl propionate, vinylidene chloride, styrene, methyl methacrylate, ethylene, and the like.
the invention is also applicable to mixtures of a vinyl halide resin in a major proportion with a minor proportion of other syn thetic resins, such as chlorinated polyethylene, polyacrylate and polymethacrylate esters, polyacrylonitrile, and terpolymers of acrylonitrile, butadiene, and styrene.
a vinyl halide resin in a major proportion with a minor proportion of other syn thetic resins, such as chlorinated polyethylene, polyacrylate and polymethacrylate esters, polyacrylonitrile, and terpolymers of acrylonitrile, butadiene, and styrene.
Any of the well-known plasticizers 'for vinyl halide resins can be used including dioctyl phthalate, dibutyl sebacate, tricresyl phosphate, and octyl diphenyl phosphate.
the stabilized resinous compositions may contain other resin additives, such as pigments, dyes, extenders, processing aids, fillers, and light stabilizers, in the amount ordinarily employed for the purposes indicated.
the stabilized vinyl halide resin compositions may be prepared by any convenient procedure. It is generally preferred to blend the stabilizer with the vinyl halide resin using plastic mixing rolls at a temperature at which the mix is fluid and to mill the composition on a two-roll mill at from 300 -F. to 400 F. for a time sufficient to form a homogeneous sheet.
the plasticizer, if one is employed, and other additives may be incorporated with the stabilizer.
the stabilized composition may then be removed from the mill in the form of a sheet or film of the desired thickness which may be used as such or subjected to a polishing or embossing treatment.
Example 1 m ea Composition Di-n-butyltin bis (mono-n-octadeeyl Modcratehaze.
Example 2 maleate
the heat stability of the compositions was determined by placing 1 x 1 specimens which had been cut from the milled sheets in forced-circulation ovens at 350 F. and 375 F. and removing specimens periodically until degradation was complete as indicated by color change.
the compositions of this invention and the comparative compositions had excellent long term heat stability; the compositions of this invention were slightly superior in early color hold to the comparative compositions.
a liquid organotin compound having the structural formula wherein each R represents a branched-chain alkyl group having from 16 to 18 carbon atoms, an alkenyl group having from 16 to 18 carbon atoms, or a hydroxy alkenyl group having from 16 to 18 carbon atoms.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)

US796900A 1969-02-05 1969-02-05 Organotin bis(monoorgano maleates) Expired - Lifetime US3637777A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US79690069A	1969-02-05	1969-02-05

Publications (1)

Publication Number	Publication Date
US3637777A true US3637777A (en)	1972-01-25

Family

ID=25169347

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US796900A Expired - Lifetime US3637777A (en)	1969-02-05	1969-02-05	Organotin bis(monoorgano maleates)

Country Status (7)

Country	Link
US (1)	US3637777A (fr)
AT (2)	AT299240B (fr)
BE (1)	BE745564A (fr)
ES (1)	ES401209A1 (fr)
FR (1)	FR2032739A5 (fr)
GB (1)	GB1273871A (fr)
NL (1)	NL7001577A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3933743A (en) *	1972-05-10	1976-01-20	Albright & Wilson Limited	Organotin thermal stabilizers for PVC resins
US3933750A (en) *	1973-05-10	1976-01-20	Albright & Wilson Limited	Novel stabilized polymer compositions
US4231949A (en) *	1978-07-28	1980-11-04	Albright & Wilson Limited	Process for preparing organotin esters

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4988750A (en) *	1981-07-17	1991-01-29	Schering Ag	Non-toxic stabilizer for halogenated polymer
FR2758141B1 (fr) *	1997-01-09	1999-02-26	Atochem North America Elf	Composition a base de maleates d'organoetain de poids moleculaire eleve utilisable pour stabiliser des polymeres thermoplastiques. procede d'obtention de ladite composition

1969
- 1969-02-05 US US796900A patent/US3637777A/en not_active Expired - Lifetime
1970
- 1970-02-04 AT AT99370A patent/AT299240B/de not_active IP Right Cessation
- 1970-02-04 AT AT622571A patent/AT304869B/de not_active IP Right Cessation
- 1970-02-04 FR FR7003965A patent/FR2032739A5/fr not_active Expired
- 1970-02-04 NL NL7001577A patent/NL7001577A/xx unknown
- 1970-02-05 BE BE745564D patent/BE745564A/fr unknown
- 1970-02-05 GB GB5649/70A patent/GB1273871A/en not_active Expired
1972
- 1972-03-27 ES ES401209A patent/ES401209A1/es not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3933743A (en) *	1972-05-10	1976-01-20	Albright & Wilson Limited	Organotin thermal stabilizers for PVC resins
US3933750A (en) *	1973-05-10	1976-01-20	Albright & Wilson Limited	Novel stabilized polymer compositions
US4231949A (en) *	1978-07-28	1980-11-04	Albright & Wilson Limited	Process for preparing organotin esters

Also Published As

Publication number	Publication date
ES401209A1 (es)	1975-02-16
GB1273871A (en)	1972-05-10
NL7001577A (fr)	1970-08-07
AT304869B (de)	1973-01-25
BE745564A (fr)	1970-07-16
FR2032739A5 (fr)	1970-11-27
AT299240B (de)	1972-06-12
DE2005291A1 (de)	1970-09-03

Legal Events

Date

Code

Title

Description

1982-12-30

AS

Assignment

Owner name: CHASE COMMERCIAL CORPORATION, 560 SYLVAN AVE., ENG

Free format text: SECURITY INTEREST;ASSIGNOR:NUODEX, INC.;REEL/FRAME:004080/0833

Effective date: 19821222

1983-03-28

AS

Assignment

Owner name: NUODEX INC.; TURNER PLACE, PISCATAWAY, NJ. 08854

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:TENNECO CHEMICALS, INC.;REEL/FRAME:004120/0362

Effective date: 19821222

1985-08-21

AS

Assignment

Owner name: NUODEX INC., TURNER PLACE, PO BOX 365, A CORP. OF

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:CHASE COMMERCIAL CORPORATION;REEL/FRAME:004444/0624

Effective date: 19850801

Publication	Publication Date	Title
US2847443A (en)	1958-08-12	Pentaerythritol products
US3591552A (en)	1971-07-06	Stabilized vinyl halide resin compositions
US3209013A (en)	1965-09-28	Oxetane ring containing phosphites
US3533975A (en)	1970-10-13	Stabilized vinyl halide resin compositions
US2935491A (en)	1960-05-03	Synergistic stabilizer composition containing a benzoate, a phenolate, and triphenyl phosphite
US3758537A (en)	1973-09-11	Bis{8 hydrocarbyl(halo)(mercapto)tin{9 oxide
US2826597A (en)	1958-03-11	Stabilizer for resins
US4111903A (en)	1978-09-05	Organotin compounds and vinyl halide resin compositions stabilized therewith
US3293273A (en)	1966-12-20	Organotin mercapto ethylene carboxylates and method for producing same
US3642846A (en)	1972-02-15	Organotin bis(monoalkenyl maleates)
JPS62111951A (ja)	1987-05-22	新規な不飽和カルボン酸エステル、その用途およびこれにより安定化された塩素化ポリマ−
US4043957A (en)	1977-08-23	Stabilized vinyl halide resin compositions
US3555060A (en)	1971-01-12	Organothio-,organocarboxy-,and organothio-organocarboxystannoxanes
US4418169A (en)	1983-11-29	Stabilized pvc resins
US3758341A (en)	1973-09-11	Halo(organo) tin thiocarboxylates
US2770611A (en)	1956-11-13	Halogenated polymers stabilized with a hexaorganodistannoxane
US3657294A (en)	1972-04-18	Process for preparing organotin mercaptides
US3202622A (en)	1965-08-24	Vinyl halide resin stabilizers comprising hydrolyzed mixtures of metal phenates, metal salts of monocarboxylic acids and organic phosphites
US3232905A (en)	1966-02-01	Vinyl halide resins stabilized with hydrocarbyl tin epoxy-alkyl succinates
US3665025A (en)	1972-05-23	Organo(halo) disulfur tin derivatives and the process of preparing the same
US3546162A (en)	1970-12-08	Ortho-ester stabilized polyvinylchloride resins
US2826561A (en)	1958-03-11	Polyvinyl chloride resin compositions containing organotin mixed salts of a fatty acid and maleic acid
US2745820A (en)	1956-05-15	Tri-butyl-tin-mono-methoxide and polyvinyl chloride resin stabilized therewith
US3650984A (en)	1972-03-21	Nitroalkane or nitroalkanol complex with alkyl-tin oxide or alkyl-tin chloride
US2687429A (en)	1954-08-24	Process of preparing succinatefumarate adducts

US3637777A - Organotin bis(monoorgano maleates) - Google Patents

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